Top 10 Unlikely Wins That Delivered Big Returns

In the world of sports betting, few things stir up more excitement, or regret, than a true underdog story. These are the moments where logic goes out the window, odds get shattered, and those who took a chance on the impossible walked away with big payouts. 

From global football upsets to surprise boxing victories, these 10 unlikely wins delivered big returns for those who backed the underdog, though few saw them coming.

1. Leicester City Wins the Premier League (2015–16)

  • Odds: 5000/1
  • Payout: £5,000 on a £1 bet

In arguably the greatest upset in football history, Leicester City defied the odds, the pundits, and conventional wisdom to win the Premier League. Starting the season tipped for relegation, Claudio Ranieri’s men wrote a modern fairy tale that rewarded brave bettors with huge returns.

2. Buster Douglas KOs Mike Tyson (1990)

  • Odds: 42/1
  • Payout: $42,000 on a $1,000 bet

Undefeated and feared, Mike Tyson seemed untouchable—until he wasn’t. In Tokyo, the 42-to-1 underdog James “Buster” Douglas stunned the world with a 10th-round knockout, causing one of the biggest shocks in boxing history.

An AI generated image of Buster Douglas fighting Mike Tyson in 1990.

3. Greece Wins Euro 2004

  • Odds: 150/1
  • Payout: £15,000 on a £100 bet

With no real superstars and a deeply defensive style, Greece wasn’t supposed to make it out of the group stage, let alone win the entire tournament. But they did—beating hosts Portugal twice in the process.

4. Holly Holm Defeats Ronda Rousey (2015)

  • Odds: 11/1
  • Payout: $11,000 on a $1,000 bet

Ronda Rousey was the queen of the UFC, unbeaten and barely challenged. Then Holly Holm came along and executed a flawless strategy, knocking her out in the second round and stunning the MMA world.

5. Japan Beats South Africa in Rugby World Cup (2015)

  • Odds: 80/1
  • Payout: £8,000 on a £100 bet

Known as the “Brighton Miracle,” Japan’s last-minute try to beat the mighty Springboks shocked rugby fans and bookmakers alike. It was Japan’s first World Cup win in 24 years.

6. Saudi Arabia Beats Argentina at the 2022 World Cup

  • Odds: 25/1
  • Payout: $2,500 on a $100 bet

Nobody gave Saudi Arabia a chance against Lionel Messi’s Argentina. But a second-half comeback and a resolute defence handed the Saudis a historic 2-1 win that rocked the footballing world.

A photo of a stand filled with Argentina fans at the 2022 World Cup supporting their team.

7. Emma Raducanu Wins the US Open (2021)

  • Odds: 400/1 (pre-tournament)
  • Payout: £40,000 on a £100 bet

Raducanu didn’t even have to qualify for Wimbledon earlier that year. Yet by the end of the summer, she’d won the US Open—without dropping a set. A teenage qualifier becoming champion? That’s jackpot material.

8. The Miracle on Ice (USA vs. USSR, 1980 Olympics)

  • Odds: 1000/1 (estimated)
  • Payout: $100,000 on a $100 bet

Team USA, made up of amateurs and college kids, toppled the Soviet Union, a hockey powerhouse that hadn’t lost in years. This wasn’t just a sporting upset; it was a geopolitical moment.

9. St. Louis Cardinals Win 2011 World Series

  • Odds: 999/1 (mid-season)
  • Payout: $99,900 on a $100 bet

Dead in the water by August, the Cardinals staged a miraculous comeback, clinched a wild card spot, and went on to win one of the most dramatic World Series in MLB history.

An AI generated image of the St Louis Cardinals celebrating their 2011 World Series win against the Texas Rangers.

10. North Korea Beats Italy (1966 World Cup)

  • Odds: Estimated 1000/1
  • Payout: £1,000 on a £1 bet

In one of football’s earliest great shocks, North Korea beat the mighty Italy 1-0, eliminating them from the World Cup and sending a ripple through the sport that still echoes today.

Final Thought: Would You Have Taken the Bet?

Hindsight makes every upset seem obvious, but the truth is, sport thrives on unpredictability & these moments remind us how rare and surprising big wins can be.

Whether you prefer to play it safe or take the occasional long shot, it’s all about enjoying the game—not chasing the win. Always gamble responsibly, and only bet what you can afford to lose.